Boron trifluoride etherate → HCID 86685118, compound

Participants

Reaction Steps

To a solution of (5-bromo-2-chloro-phenyl)-(4-ethoxy-2,3-difluoro-phenyl)methanone 23d (17.6 g, 46.8 mmol) in acetonitrile (100 mL) was added triethyl silicane (18.7 mL, 117.1 mmol) at 15° C., and then boron trifluoride diethyl ether (28.9 mL, 234.1 mmol) was added. The mixture was warmed up to room temperature and stirred for 15 hours. The reaction mixture was adjusted with saturated aqueous sodium bicarbonate to pH 7 and extracted with ethyl acetate (150 mL×3). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE to give the title compound 23e as a white solid (9.45 g, 63%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ(ppm): 7.34-7.30 (m, 1H), 7.29-7.26 (m, 2H), 6.79-6.75 (m, 1H), 6.71-6.66 (m, 1H), 4.12 (q, 2H), 4.04 (s, 2H), 1.47 (t, 3H).

Provenance & Evidence